Acetic Acid → Hydrochloric Acid
Reaction equation
[ClH:1].[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[N:11][C:12]([C:30]([NH2:32])=[O:31])=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:23])=[CH:18][CH:17]=3)[N:14]=2)[CH2:4]1.CCN(C(C)C)[CH:36]([CH3:38])[CH3:37].CC(C)=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O1CCOCC1.O>[CH:36]([NH:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[N:11][C:12]([C:30]([NH2:32])=[O:31])=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[O:23])=[CH:20][CH:21]=3)[N:14]=2)[CH2:4]1)([CH3:38])[CH3:37].[ClH:1]Participants
10
Reactant 5
Product 2
Reagents, catalysts & solvents 3
Procedure
To a solution of (R)-3-(3-aminopiperidin-1-yl)-5-(4-(morpholine-4-carbonyl)phenylamino)-1,2,4-triazine-6-carboxamide HCl salt (100 mg, 0.21 mmol) in 1,2-dichloroethane (10 mL) and dioxane (10 mL) was added DIEA (0.18 mL, 1.05 mmol) and then acetone (0.31 mL, 4.2 mmol). The mixture was stirred for 3 h at RT. To the mixture was added HOAc (0.12 mL, 2.1 mmol) and then NaBH(OAc)3 (223 mg, 1.05 mmol). The mixture was stirred at RT overnight and then water (2 mL) was added. The mixture was concentrated in vacuo and subjected to reverse phase preparative HPLC to afford the title compound as HCl salt (50) (17 mg). MS found for C23H32N8O3 as (M+H)+ 469.2, (M−H)− 467.3. UV: λ=268 nm.
Workup
- stirringThe mixture was stirred at RT overnight
- concentrationThe mixture was concentrated in vacuo
Sources & evidence
- ORD record
- ord-d0d9a54a653e472faec52ca6eceeb0fb
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382246B2
Reaction notes
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